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Synthesis 1996; 1996(1): 105-110
DOI: 10.1055/s-1996-4154
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Tricarbonyls: Reactive Model Dienophiles for Asymmetric Diels-Alder Reactions

Hans-Joachim Lehmler1 , Martin Nieger2 , Eberhard Breitmaier1
  • 1Institut für Organische Chemie und Biochemie der Universität Bonn, Gerhard-Domagk-Straße 1, D-53121 Bonn, Germany, Fax +49(228)735683
  • 2Institut für Anorganische Chemie der Universität Bonn, Gerhard-Domagk-Straße 1, D-53121 Bonn, Germany
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Publication History

Publication Date:
31 December 2000 (online)

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The hetero-Diels-Alder reaction of 2-methyl-1-(1-phenylalkoxy)-butadienes 5a-d with cyclic triketones proceeds smoothly at room temperature in excellent yield and high diastereoselectivity. The configuration of the cycloadducts 6a and 6b was determined by X-ray single crystal analysis. Mild acidic hydrolysis of the cycloadduct 6a using SiO2 as a promoter yielded an α,β-unsaturated aldehyde trans-9. The trans-epoxides 10a-d can be obtained from 6a-d using a freshly prepared solution of dimethyldioxirane in acetone.

hetero-Diels-Alder reaction - 2-methyl-1-(1-phenylalkoxy)-1,3-butadienes - indanetrione - alloxane - dimethyldioxirane

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